


A Heavenly Engagement

by CharlotteEtienne24601



Category: Supernatural
Genre: Bad Parent John Winchester, Coming Out, Dean Winchester Has Internalized Homophobia, Eileen Leahy Ships Castiel/Dean Winchester, Engagement, F/M, Getting Together, Homophobia, John Winchester's A+ Parenting, M/M, Marriage Proposal, Mary Winchester Ships Castiel/Dean Winchester, Post-Episode: s15e20 Carry On, Sam Winchester Ships Castiel/Dean Winchester
Language: English
Status: In-Progress
Published: 2020-11-29
Updated: 2020-12-01
Packaged: 2021-03-09 20:22:22
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 2,265
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27782170
Author URL: https://archiveofourown.org/users/CharlotteEtienne24601/pseuds/CharlotteEtienne24601
Summary: After Sam and Eileen get engaged in Heaven, Sam persuades Dean to finally talk with Cas.
Relationships: Castiel/Dean Winchester, Eileen Leahy/Sam Winchester
Comments: 9
Kudos: 39





	1. Beginnings

**Author's Note:**

> This will be maybe three chapters, and I have the second one written. Dean and Cas will eventually get married, although this first chapter is mostly them finally getting together.
> 
> Also, comments make me really happy and convince me that people actually like my writing, so if this makes you happy, consider commenting!   
> Otherwise I'll just continue screaming into the void (the Empty?) for my own amusement, that's fine too. :D

Soon after reuniting in Heaven, Sam and Eileen got engaged. With the fluidity of time there, though, there was no particular rush to have the ceremony, and they took their time planning it.

One day, Sam was over at Dean’s hanging out and drinking beer when the subject turned to the wedding.

“I’m really proud of you, Sammy. You get your happily ever after, you’re going to have forever with Eileen...it’s really good that one of us is that happy.”

Sam grinned over at him. “Thanks, man. I love her so much.” His eyes practically glowed with hearts.

“Yeah, I know you do, bitch.”

“Jerk,” Sam paused. “Dean, you know you should be happy too, right?”

Dean shrugged. “Eh, I’m in Heaven. What could be better?”

“Have you thought any more about contacting Cas?”

“Why would I contact Cas? He’s busy, and if he doesn’t want to come around, then I’m not gonna force him.”

Sam rolled his eyes. “Get over yourself, Dean. You obviously love him.”

Dean shifted uncomfortably. “What makes you say that?”

“It’s always been really obvious, honestly. The two of you were always really close, and even when you were fighting, you were always thinking of and caring for each other. Also, you made the most eye contact of anyone, ever. And you stopped hooking up with random people as much once he was in your life.” He hesitated. “And he was really in love with you, too.”

Dean, who had never told Sam about Cas’s confession, choked on his beer. “Why would you think that??”

“Again, obvious. I don’t know why you’re so set against talking to him, but I think you should. In fact, maybe I just won’t leave until you contact him.”

Dean sighed. “He won’t come when I call, anyway.”

“Yeah, I really think he will. Anyway, if you try it and he doesn’t, I’ll drop it.”

Dean rolled his eyes. “Fine. Uh, Cas, I hope you’ve got your ears on. I’d...I’d like to see you, man. And Sammy’s here, he’s not going to shut up until you get down here. Or, up here? Whatever. Just...we want you here, buddy.” He paused. “So yeah, you see? He’s not gonna show up.”

“Hello, Dean.” Cas spoke up from where he had materialized next to Dean.

Dean lept to the side and stared at him. “What the Hell, man?”

“You called. I answered.”

“Cas, man, it’s good to see you!” Sam said, grinning and pulling Cas into a hug. Dean continued staring mutely, and Sam turned to him. “Dean, would you like to greet Castiel?”

“Uh. Hey, Cas,” Dean mumbled.

“It’s good to see you, Dean.”

Dean shuffled his feet. “Yeah, uh, good to see you, too.”

Cas frowned. “Was there something you needed?”

Dean shook his head. “Sam just wanted to see you, but you don’t have to stick around.”

Cas pursed his lips. “Okay.”

“For goodness’ sake,” Sam said. “Look, Cas, you and Dean need to talk, okay? I know you don’t want to admit that you’re in love with each other or whatever, but come on, it’s been years and you’re literally in Heaven now. Get your shit together.”

Cas looked down at his shoes. “I already did.” He said quietly.

Sam stared. “I’m sorry, what?”

Cas sighed. “I see Dean has not filled you in.”

Dean looked uncomfortable as Sam turned to him. “What the Hell, Dean?”

“Look, man, it’s not important and it’s none of your business, okay?”

Cas looked stung. “Dean, if you do not reciprocate, I understand, but it is important to fill your brother in on the important events of your life.”

Dean sighed. “It’s not that, Cas, it’s just…” he trailed off.

“Dean, is this still about the guy thing?” Sam asked gently.

“Like I said, it’s none of your business, man.”

Sam rolled his eyes, giving his best bitchface. “You’re in literal Heaven and you’re not going to let yourself be bi?”

“I’m not...come on, Sam.”

“Okay, even if you stay in denial about that for the rest of your, uh, death; this is  _ Cas _ , man.”

“So what do you want me to do? Tell him I love him too and ask him to be my boyfriend or something?”

Sam nodded. “Yeah, that’s remarkably close to what I was thinking, actually.”

Cas spoke up. “Sam, if Dean does not share my affections or does not wish to act on them, it is best that we respect his needs.”

Sam sighed. “Dean, this is an angel telling you he loves you, and he literally jumped into a void to save you after baring his soul to you.”

“My soul was very much shielded, Sam.” Cas intoned.

“It’s not...it’s a figure of speech, Cas. Anyway, Dean, are you really going to let him get away?”

Dean sighed. “I...Cas, I...look, Sam might have a point.”

“Really?” Cas looked at him hopefully. Dean nodded, looking nervous. Cas pulled him into a tight hug, resting his chin on Dean’s shoulder. “I never thought this would happen.”

“Yeah, well. I guess it is.” Dean patted Cas’s back.

After a moment, Cas shifted. “May I kiss you?”

Dean hesitated. “Er...yeah. Yeah, you can.”

Cas broke out in a bright smile. “Thank you, Dean.” He gazed into Dean’s eyes for a moment.

“Man, you can’t  _ thank _ people for letting you kiss them…”

Cas cocked his head. “But you are allowing me something that I have wanted for many years. It seems to me that thanks is deserved.”

“Cas, man, just…” Dean leaned forward and caught Cas’s lips in a gentle kiss.

Sam whooped, and Dean flipped him off without moving away from Cas. “Well, I’ll leave you two alone. Call me sometime when you get a chance.” Sam smirked and left the house.

After a few minutes, Cas pulled back. “Dean, I love you.”

Dean smiled. “I...me, too, Cas.”

“I do not understand all the intricacies of why this is difficult for you, but I understand that it is. How can I make this more comfortable for you? I want you to be happy.”

Dean considered this. “Uh. My dad taught me that men don’t, um. Do stuff with each other. So that might take me awhile. I  _ want _ to, I just...it’s hard to be comfortable with that, you know?”

“Dean, we never have to have sex if you do not want to.”

Dean laughed, patting Cas on the shoulder. “I appreciate that, Cas, but I really, really want to have sex with you. It’s just probably going to take me some time.”

Cas nodded. “We will not go beyond your comfort level. We can explore the romantic side of our relationship for awhile instead.” He kissed Dean on the forehead.

“Uh, actually.” Dean cleared his throat. “Romantic stuff isn’t really in my wheelhouse, either. Like, I want that stuff with you, but it’s not really what I know how to do, you know? I had that thing with Lisa, but it’s not like I’ve had a lot of experience with it other than that.”

Cas nodded slowly. “I must admit that I do not know where to start in order to make you comfortable.”

Dean huffed a laugh. “Yeah, I know, I’m sorry. Let’s just, I dunno. Kiss a lot and take it from there?”

And so they did, spending the next several months getting to know each other in new ways and enjoying their newfound domesticity.


	2. Chapter Two

**Summary for the Chapter:**

> Dean considers marriage and comes out to his parents.

**Notes for the Chapter:**

> Warning this chapter for John being a homophobic asshole.

When Dean told Bobby, he smirked. “Finally. I thought you two would never pull yourselves together.”

“Oh, come on, Bobby…”

“You and that angel been dancing around each other for so many years now. It’s good to see you happy, Dean.” He clapped Dean on the shoulder.

Dean smiled and blushed. “Thanks, Bobby. I...yeah, it’s good. I’m happy.”

“I’m happy for you, son.” He pulled Dean into a hug.

One day, when Dean and Eileen were spending some time together, he brought up marriage.

“Hey so I wanted to ask you…”

“Hmm?”

“You and Sam, you’re like...you’re solid, right?”

“We are. I love him very much.”

“How did you decide it was the right time to get engaged?”

She smiled. “It just felt right, at some level. I know he’s my priority and I want to come home to him each day, and I want to have a public recognition of our love.”

Dean nodded slowly. “Okay. Okay, yeah, that makes sense.”

“Dean, you’re sweating. Are you okay?”

“I just, you know. I was thinking about asking Cas to marry me.”

She grinned. “You should do that!”

“But, I dunno, what if he doesn’t want to?” He asked, looking down at his shoes.

“Dean, you have to look at me, remember?” He turned towards her and repeated his question. She laughed. “He very obviously does. You should just ask him. I’m sure he’ll say yes.”

“I hope so.” He shifted awkwardly. “Uh, if I do this, I also have to tell my parents.”

She nodded. “Yes, you do.”

“I don’t know if you know this about us, but our dad, he…” he trailed off.

“He’s a homophobic asshole? Sam told me.”

Dean hesitated. “Look, things were hard for him, raising the two of us on his own…”

“I know. That doesn’t mean he had to teach you those things.”   
“Yeah, I guess so.”

She hugged him. “We’ll back you up, Dean. I know Sam would agree with me. If he says  _ anything _ …”

He smiled sadly. “Thanks, Eileen. That means a lot.”

“I’ve gotta support my brother, don’t I?”

Dean summoned up his courage and went to visit his parents alone one day.

After they chatted and caught up a little bit, he cleared his throat. “So, I haven’t told you this, but Cas and me are a thing.”

Mary smiled. “I know.”

“You  _ know _ ??” Dean and John both cried.

Mary rolled her eyes. “Yes, Dean. It’s been pretty obvious since I first met Cas and saw the two of you interact.”

“Apparently everyone but me thought it was super obvious.” Dean sighed.

She shrugged. “I’m glad you figured things out.”

John cleared his throat uncomfortably. “So what, you’re gay now? After everything I taught you?”

Dean sighed. “I’m not  _ gay _ , it’s just…”

Mary got there first. “John Winchester, did you raise your children to be homophobes?”

“It’s not homophobic, Mary, it’s just not how things are supposed to be…”

“You can leave this house if that’s what you think.” She snapped.

Dean stared. “Mom, it’s not…”

“Oh, yes it is.” She glared at John. “You can either support your son or you can get the hell out of our lives.”

John blinked. “Mary…”

“You’d better make your decision and be done with it.” She turned to Dean, her face softening. “You should bring Cas over for dinner sometime soon. I’d love to get to know him.”

“Thanks, Mom.”

John stood up. “I need some time with this. I’m gonna go take a walk.” He turned to Dean. “Uh, it was good to see you, son.”

Dean nodded, looking awkward. “Yeah, uh. You too.” After John left, Dean turned back to Mary. “So um, there’s something else.”

“Oh, really?” She looked at him curiously.

“Yeah, um. I think I’m gonna ask him to marry me.”

“That’s wonderful, Dean.” She smiled, then paused. “John will come around. Probably. And if he doesn’t, I’m serious about sending him away. Nobody treats my kid like that.”

Dean smiled sadly. “I...thanks.”

She got up and hugged him. “I’m serious about being a better parent to you now. You know that, right?”

“Yeah, I do.”

Dean spent a lot of time mulling over how he would ask Cas. Should he do something showy? That wasn’t really Cas’s style. But would that be different for something this big?

In the end, he decided to go with something quiet and simple. The nice thing about Heaven was that things you needed just seemed to sort of appear when they were wanted. One day when he was at the kitchen table nursing a beer, Cas having already gone to bed, he noticed a ring sitting on the table next to him and realized it was perfect for Cas.

The next night, he and Cas were snuggled up on the couch together watching a movie, Cas leaning back between Dean’s legs. As the movie ended, Dean paused it.

“Hey, Cas?”

“Mmm?” Cas made an inquisitive noise, turning his head to kiss Dean’s jaw.

“I was wondering. Um.”

“What is your question, Dean? You know you can ask me anything.”

“I, uh. Castiel, will you marry me?”

Cas’s face broke out into a sunshiny smile. “Of course I will, Dean.”

“What, really?”

“Did you think I’d say no?”

“Uh, not really, just. Never thought I’d have this, you know.”

Cas turned in Dean’s arms so he could kiss him. “You have me, Dean. Forever.”

When Dean told Sam, his brother pulled him into a big hug. “I’m proud of you, Dean. You went after what you wanted, even though it was hard for you.”

“Thanks, man.”

Sam beamed at him. “Hey, we could have a double wedding!”

Dean rolled his eyes. “Really, dude?”

“I mean, we would have to talk with Eileen and Cas, but I think they’d be up for it.”

“Why do you want this?”

Sam shrugged. “We’ve always done everything together. It just seems like we should start this next stage of life, er, death, together too.”

Dean smirked. “Yeah, that’s true enough. Okay, if Eileen and Cas are on board, so am I.”


End file.
